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2-Butenal

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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltafgas-109.7 ± 2.4kJ/molCcbVan-chin-syan, Kochubei, et al., 1996ALS
Deltafgas-106.9kJ/molN/ATjebbes, 1960Value computed using «DELTA»fHliquid° value of -144.1±0.4 kj/mol from Tjebbes, 1960 and «DELTA»vapH° value of 37.2 kj/mol from Van-chin-syan, Kochubei, et al., 1996.; DRB
Deltafgas-100.5 ± 1.5kJ/molChydDolliver, Gresham, et al., 1938Heat of formation derived by Cox and Pilcher, 1970; ALS

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid-146.9 ± 2.4kJ/molCcbVan-chin-syan, Kochubei, et al., 1996 
Deltafliquid-144.1 ± 0.4kJ/molCcbTjebbes, 1960 
Deltafliquid-138.6 ± 1.9kJ/molChydDolliver, Gresham, et al., 1938Heat of formation derived by Cox and Pilcher, 1970
Quantity Value Units Method Reference Comment
Deltacliquid-2284.7 ± 2.3kJ/molCcbVan-chin-syan, Kochubei, et al., 1996Corresponding «DELTA»fliquid = -146.8 kJ/mol (simple calculation by NIST; no Washburn corrections)
Deltacliquid-2287.4 ± 0.4kJ/molCcbTjebbes, 1960Corresponding «DELTA»fliquid = -144.1 kJ/mol (simple calculation by NIST; no Washburn corrections)

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C4H5O- + Hydrogen cation = 2-Butenal

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar1484. ± 8.8kJ/molG+TSBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1456. ± 8.4kJ/molIMREBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B

(CAS Reg. No. 64724-02-3 bullet 42949672952-Butenal) + 2-Butenal = CAS Reg. No. 64724-02-3

By formula: (CAS Reg. No. 64724-02-3 bullet 4294967295C4H6O) + C4H6O = CAS Reg. No. 64724-02-3

Quantity Value Units Method Reference Comment
Deltar253. ± 9.2kJ/molN/AAlconcel, Deyerl, et al., 2001gas phase; B
Deltar256. ± 10.kJ/molTherZimmerman, Reed, et al., 1977gas phase; B

Hydrogen + 2-Butenal = Butanal

By formula: H2 + C4H6O = C4H8O

Quantity Value Units Method Reference Comment
Deltar-104.2 ± 0.42kJ/molChydDolliver, Gresham, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -105.3 ± 0.4 kJ/mol; At 355°K; ALS

2-Butene, 1,1-dimethoxy- + Water = 2-Butenal + 2Methyl Alcohol

By formula: C6H12O2 + H2O = C4H6O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar15.3 ± 0.2kJ/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Van-chin-syan, Kochubei, et al., 1996
Van-chin-syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z., Thermodynamic properties of some acids and aldehydes of the acrylic series, Sov. J. Chem. Phys. (Engl. Transl.), 1996, 70, 1789-1794, In original 1932. [all data]

Tjebbes, 1960
Tjebbes, J., Heats of combustion of butannal and some related compounds, Acta Chem. Scand., 1960, 14, 180-188. [all data]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [all data]

Alconcel, Deyerl, et al., 2001
Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E., Effects of alkyl substitution on the energetics of enolate anions and radicals, J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431 . [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]

Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H., Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria, J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References